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No.30 (1983/11) >

Title :O-(2-Ethylphenyl) O, O-Diphenyl Phosphate から 4-Alkylidene-1,3,2-benzodioxaphosphorinane 2-Oxide 類の代謝生成(農芸化学科)
Title alternative :Metabolic Formation of 4-Alkylidene-1,3,2-benzodioxaphosphorinane 2-Oxides from O-(2-Ethylphenyl) O, O-Diphenyl Phosphate (Department of Agricultural Chemistry)
Authors :多和田, 真吉
Authors alternative :Tawata, Shinkichi
Issue Date :19-Nov-1983
Abstract :O-(2-Ethylphenyl) O, O-diphenyl phosphateのラット及びマウス体内での代謝により, 2-ace-tophenyl類, 2-(α-hydroxyethyl)phenol, 及び少量の4-alkylidene-1,3,2-benzodioxaphosphorin 2-oxideが代謝生成される事を^<31>PNMR及びTLC法で確認した。最終産物の4-alkylidene類は環状であると同時にエノールリン酸類の構造も有しており, 2-置換-benzo-dioxaphosphorin 2-oxide(sa-lioxon)及び2-chloro-1-(substituted-phenol)ethenyl dialkyl phosphate(例えば殺虫剤tetra chlorvinphos)の構造的特徴及び生物活性的性質をかね備えている。毒性発現及びエステラーゼ阻害はsalioxonの場合, P-O-aryl結合の反応性によるが, 4-alkylidene類の高い活性発現は, アルカリ加水分解によりP-O-ethenyl結合が切れる事から, おそらくこの部位で酵素をリン酸化するためと思われた。
O-(2-Ethylphenyl) O, O-diphenyl phosphate and O, O-di (2-ethylphenyl) phenylphosphonate are metabolized in rats and mice to give its 2-acetophenyl derivatives, 2-(α-hydroxyethyl) phenol, and small amounts of 4-alkylidene-1,3,2-benzodioxaphosphorin 2-oxides. The alkylidene derivatives are both cyclic and enol phosphates, thereby combining some structural features and biological properties of 2-substituted-benzodioxaphosphorin 2-oxides and 2-chloro-1-(substituted-phenol) ethenyl dialkyl phosphate (e. g., the insecticide tetrachlorvinphos). The toxicity and esterase inhibition are attributable to the reactivity of the P-O-aryl bond of salioxon, but the high biological activity of 4-alkylidene derivative is probably due to their action in phosphorylating esterases or proteases by the P-O-ethenyl bond cleavage, because the alkylidene cyclic phosphonates yielded O-(2-alkylketophenyl) O-methyl phenyl phosphonates on alkaline methanolysis.
Type Local :紀要論文
ISSN :0370-4246
Publisher :琉球大学農学部
URI :http://hdl.handle.net/20.500.12000/3995
Citation :琉球大学農学部学術報告 = The Science Bulletin of the Faculty of Agriculture. University of the Ryukyus no.30 p.217 -226
Appears in Collections:No.30 (1983/11)

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